Waterinsoluble disazodyestuffs



Patented Dec. 26, 1933 WATERINSOLUBLE JDISAZODYESTUFFS Heinrich Clingestein, Cologne, and Karl Dobmaier,

Leverkusen-on-the-Rhine, Germany,

assignors, to General Aniline Works, Inc., New York, N.Y.,'"a corporation of Delaware N Drawing. Application December 4, 1929,

Serial No. 411-;669wan'd in Germany December 8 iGlaims.

r 1 The, present invention .i elateslto new, water- V T- insoluble, ydisrazod dyed therewith. M V

In accordance with the present invention, waterinsoluble dis-azodyestuffs, dyeing yellow yestufis and to the materials shades are obtainable by coupling witha di-" 1 benzophenone, which may be "substituted in the nuclei, for example by halogen, methyl or methoxy, but which should not be substituted by a carboxylic acid-, sulfonic acid-, or hydroxy group.

and developed fQ1i1 abOlll'/,., /2 hour 'in'a diazo bath, rinsed, soaped at the boil, rinsed and dried.

For dyeing 50 grams of cotton, the grounding liquor is prepared by dissolving together about /2 gram to about 5 grams of the di-(aceto a'cetic arylide) about 1 to about c. c. caustic,soda lye of 34 B., and about 1 to about 10 c. 0. Turkey red oil of 150% strength,;;afnd making up the whole 'with Waterto 1 liter...v

Thetdeveloping batlrfis prepared by diazotizing ,about 1 gramtoabout-3-gliams of the orthoaminobenzophenone with about 1 to about 31;. c. of hydrochloric acid of 22 B. and a-bout 3'.to about-9 c. c. of sodium nitrite 1110, while 0001f Our new dyestuffs may be represented by the ing with ice. When diazotization is complete ,i llowing mgeneral iormula: p y g y theliquid ,isneutralized with about l to about" New rraene ww 29 v =0 =6 as" Q 0 5H3 6 wherein R stands for an aromatic nucleus, such/ C. 0. of Sod ac ate 115, whereupon 0 y as a benzene or naphthalene nucleus, and where grams of common salt are added, and the whole in the nuclei may contain substituents with the g ad p w Water to 1 t excepti0n of a carboxylic acid-;-sulfonic acid er h following eXamples serve to illustrate 011 hydroxyflgr'qup. 1 'invention, without limiting it thereto. In their 3 dry pulverized for th i dye- Example 1.--Well boiled and dried cotton yarn stuffs are generally yellow powders; 'they are in-y oisirnpregnated with an alkaline solution con- "r soluble in water, soluble in sulfuric acid and yield tamlng D l upon reduction with stannous chlorideland hy 12 grams of diacetoacetic-o-tolidide, drochloric acid the starting ortho -aminobenzo 20 c. c. of caustic soda 34 B., l;:phenoneaand.za;diataminoacetosacetic arylide). 25 c. c. of Turkey red oil, 7 1 M Theydyeingsapreparedsonlthe fiberaare'distinn v and-nevempedwithout g in albino ishe y an excellent fastness to washin bath of. diazotized-o aminobenzophenone to? chlorine kler bmhng- Whitin odi mac tat rhas een ad h o p s the dyestuffison h flb D ton is thereby dyed an intense pure greenish cially on cotton, the materlal to-be-dyed is imyellow. The dyeing is remarkablyfast-to-light, 40 pregnated w1th a groundmg liquor, containing kier boiling, chlorineand washing. The dye g the diracem'ittfie i as f e lwmn a 'fiil l hfl thepmb e r ula; 9 r cm 0H3 -I -on ({H d=o N=NZ JHa r h y .4 vfastnessto washing, chlorine and kier boiling. ample 1 but mg thereby 4 m Z DiS-aZOdYGStUfiS of the general formula:

NH-C=O.N=N

V 43KB diphenyl-ketone and diaceto-o-tolidide, a yellow wherein the nuclei may contain substituents with 95 is obtained The dyestufil has the probable forthe exception of a 'carboxylic 'acid -,"sulfonic acid- J niulazfi "and "hydroxy group, 'beinginsoluble inwater,

' 'N=N g 3 1 (J H:

Bystreating the dyestuff with hydrochloric acid soluble in sulfuric acid, and dyeing yellow shades and stannous chloride it yields di-(aminoracetoof good fastness to washing, chlorine and kier acetic-o-tolidide) and 4-mcthyl-2flaming-di boiling. I g V I phenyl ketone. a. v 3'. Thedis-azodyestuff of the formula "a Q 7011., Les. 4 6

7 .9 O/H =0 x 1,1 i=0 I Hz l 1 ,''We claim:-- being insoluble in water, soluble in sulfuric acid,

1. Dis-azodyestuffs and dyeing yellow shades of good fastness to 7 (i): I 0 0 72 I a r '135 wherein R stands for anammatic nucleus of washing, chlorine and kier boiling. I the benzene or naphthalene series and wherein 4. The disazo dyestufi of the formula:

By treating the dyestuff with hydrochloric acid and stannous chloride it yields di-(amino-acetoacetic-o-tolidide) and-o-aminobenzophenone.

Example 2.When working as outlined in Exthe nuclei may contain substituents with the exception of a carboxylic acid-,. sulfonic acidand hydroxy-group, being insoluble in water, soluble in sulfuric acid, and dyeing yellow shades of good of the general formula:

said dyestuff being insoluble in water, soluble in sulfuric acid and dyeing yellow shades oigood claim 3.

fastness to washing, chlorine and kier boiling. 8. Fiber dyed with the dyestuff claimed in 5; Fiber dyed with the dyestufi claimed in claim 4. claim 1.

6. Fiber dyed with the dyestufi claimed in claim 2.

KARL DOBMAIER.

'7. Fiber dyed with the dyestufi claimed in 

